Yarn treating process and composition therefor



Patented May 7, 1940 PATENT OFFICE YARN TREATING PROCESS AND COMPOSITION THEREFOR Joseph B. Dickey and James B. Normington, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application November 26, 1937, Serial No. 176,695

14 Claims.

This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of oranic derivatives of cellulose such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, etc., to render them more amenable to textile operations such as knitting and the like.

As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. In addition, it is necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various' types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as stitch distortion, pin holes, laddering, and the like.

Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufflcient solvent power for the lubricants with which they are used and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening and lubricating agents are insufficiently soluble in water to permit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely new class of yarn conditioning lubricants when applied to such yarns. A still further object is to provide yarn softening and lubricating formulas which can be readily removed from the yarns by the usual scour baths. A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including knitting, weaving, spinning and the like. Still another object is to provide new chemical compounds having the structure and properties discussed below. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that keto-ethers having the general formula:

where R. is an alkyl group; R may be hydrogen, or an alkyl; R" is an alkoxy alkyl or heterocyclic group, and R' is an'alkyl group, may be used as yarn conditioning agents and particularly as softening agents, with or without the addition of animal, mineral or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose. We have found that these compounds have a slight solvent and/or softening action on cellulose organic derivative yarns which renders such yarns soft and pliable without at the same time having too drastic a solvent action thereon.

In accordance with the invention these compounds may be applied directly'to the yarn during or after spinning, or may be added to the spinning solution itself. We have found that these compounds have exceptional solvent powers which enable them to dissolve mineral oils and blown and unblown, drying and semi-drying vegetable and animal oils and accordingly they may be, and preferably are, employed as ingredients of yarn conditioning or lubricating formulas in conjunction with agents which function wholly or partially as lubricants.

In the following examples and description we have set forth several of the preferred embodiments of our invention, but they are included merely for purposes of illustration and not as a limitation thereof.

Although the keto-ethers of the above-indicated specific structural formulas are now compounds, their preparation may be carried out in general accordance with the article by Alfred Hofiman appearing on page 532 of volume 49 of the Journal of the American Chemical Society. For example, diacetone methoxy ethyl ether may be prepared by allowing 4 moles of mesityl oxide, 10 moles of methoxy ethanol, and 20 grams of concentrated sulfuric acid to stand at 20 to 30 degrees for ten to twelve days. Twenty-five grams of lime are then added and the mixture stirred on the steam bath for one hour until neutral. Fractionation gives the ether, a yellowish oil, with a boiling point -110/17 mm.

Similarly the preparation of diacetone tetrahydrofurfuryl ether may be carried out by allowing 4 moles of mesityl oxide, 8 moles of tetrahydrofurfuryl alcohol, and 20 grams of concentrated sulfuric acid to stand at 25 degrees for ten to twelve days. The solution is worked up as before yielding the ether with a boiling point -120/13 mm.

Our invention will be more readily understood by reference to the following examples in which typical applications of the invention are set forth:

Example I.-A 20% solution of cellulose acetate in acetone in which is incorporated 1-25% by weight of the cellulose acetate of 4-methyl- 4(18-methoxyethoxy)pentanone-2 is extruded through orifices into an evaporated atmosphere.

The filaments thus produced are wound, or

twisted and wound. Yarns produced from filaments thus prepared are pliable and especially well adapted for knitting.

Example II.Yarn designed for knitting and composed of cellulose acetate is treated by applying thereto diacetone tetrahydrofurfuryl ether by means of an applicator roll. The amount of the conditioning liquid may run from 4 to 25% by weight of the untreated yarn. If the yarn is intended for weaving, the same procedure may be followed, except that the amount of conditioning agent added to the yarn is only about 1 to 5%.

Example III.A conditioning liquid is made up by mixing the following ingredients in the indicated proportions:

Per cent 4-ethyl-4(/3-ethoxyethoxy) pentanone-Z 70 Olive oil 30 This composition is applied to a cellulose acetate yarn intended for knitting in an amount repre senting 4 to 25% by weight of the untreated yarn. The filaments or fibers treated as described above are quite soft and pliable and give excellent results in textile operations, especially in knitting.

Other examples of yarn conditioning compositions which may be applied to various types of yarn, particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate and similar cellulose organic acid esters, in accordance with our invention, and which render such yarns soft and pliable and especially well adapted for various textile operations, particularly knitting, are the following:

Example IV Per cent 4-methyl-4(tetrahydrofurfuryl oxy-) hexanone-2 60 Blown olive oil 40 Example V 4-tetrahydrofurfuryl oxy pentanone-2 '70 Neats-foot oil 30 Example VI 4-,8-ethoxy-,8-ethoxyethoxy hexanone-2 '70 Light mineral oil 30 Example VII 4-methyl-4 (p'-butoxy-5-ethoxyethoxy) pentanone-2 70 ,Blown neats-foot oil 30 Example VIII Diacetone tetrahydrofurfuryl ether 50 Sperm oil 50 Example IX 4-methyl-4-(fl-methoxyethoxy) pentanone-2 70 Blown sperm oil 30 Example X 4-methyl-4 (,B-methoxyethoxy) pentanone-2 l0 Blown olive oil 60 Mineral oil 30 Example XI Diacetone tetrahydrofurfuryl ether 10 Tetrahydrofurfuryl oleate 20 Mineral oil 20 Sperm oil 50 Example XII 4 methyl 4(tetrahydrofurfuryl oxy) hex- As will be apparent from the above examples and description, the conditioning agents of our invention may be applied by a Wide variety of methods. For example, we may employ the agent as an ingredient of the spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of-factors, such as the particular cellulose derivative used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.

If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll, or felt wet therewith or the liquid may be applied by immersion, spray, or otherwise. The particular point at which the liquid is applied may vary. It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and the godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by the socalled bobbin to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon the results desired, the specific nature of the material to which the agent is applied, the use to which the yarn is acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.

Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending agents and the like, may be added within the scope of our invention. Likewise, various dyes or other col- .oring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.

Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient.

While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the conditioning agents and formulas described herein are applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.

The term yarn as used hereinand in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread,,either of high or low twist,

, single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.

As indicated above, the yarn conditioning agents of our invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neats-foot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying-composition.

The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such' as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the yarn material. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal and vegetable oils and their ability to act as lubricating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.

What we claim and desire to secure by Letters Patent of the United States is:

1. The process of conditioning yarn to render it more amenable to textile operations including knitting, weaving, spinning, and the like which comprises applying thereto a lubricating and softening component a keto-ether having the general formula:

where R is an alkyl group; R is a substituent selected from the group consisting of hydrogen and alkyl; R." is an organic radical selected selected from the group consisting of alkoxy alkyl and heterocyclic groups; and R is an alkyl group.

3. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a ketoether having the general formula:

where R is an alkyl group; R is a substituent selected from the group consisting of hydrogen and alkyl; R" is an organic radical selected from the group consisting of alkoxy alkyl and heterocyclic groups; and. R' is an alkyl group.

4. The process of conditioning-yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which -comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component a ketoether having the general formula:

where R is an alkyl group; R is a substituent selected from the group consisting of hydrogen and alkyl; R" is an organic radical selected from the group consisting of alkoxy alkyl and heterocyclic groups; and R' is an alkyl group, and a textile lubricant.

5. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component 4-methyl-4 (fi-methoxyethoxy) pentanone-2.

6. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning and the like, which comprises applying thereto a lubricating and softening component diacetone tetrahydrofurfuryl ether.

7. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like, which comprises applying thereto a lubricating and softening component 4-methyl-4(tetrahydrofurfuryl oxy-) hexanone-2.

8. Textile yarn amenable to textile operations including knitting, weaving, spinning, andthe like impregnated with a lubricant containing a keto-ether having the general formula:

R(JCH2GOR where R is an alkyl group; R is a substituent selected from the group consisting of hydrogen and alkyl; R" is an organic radical selected from the group consisting of alkoxy alkyl and heterocyclic groups; and R is an alkyl group.

9. Textile yarn composed of or containing organic derivatives of cellulose amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a-conditioning agent comprising a keto-ether having the general formula:

R+CHn-COR' where R is an alkyl group; R is a substituent selected from the group consisting of hydrogen and alkyl; R" is an organic radical selected from the group consisting of alkoxy alkyl and heterocyclic groups; and R'." is an alkyl group.

11. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising 4-methyl-4(B-methoxyethoxy) pentanone-2.

12. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning and the like, impregnated with a lubricant comprising diacetone tetrahydrofurfuryl ether.

13. Textile yarns composed of or containing a cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising 4- methyl-4(tetrahydrofurfuryl oxy-) hexanone-2.

14. As a new chemical compound, 4-methyl-4 (fl-methoxyeth'oxy) pentanone-2.

JOSEPH B. DICKEY. JAMES B. NORMINGTON. 

